Learn with Phoebe Β· AI & LLMs

Learn Asking the Right Questions as an AI Developer with Phoebe

An operations director says: "Can AI answer the supplier WhatsApps?" It sounds like a technical request, and the AI developer who treats it as one builds an assistant that says yes to a substitute drug nobody checked. Most of what goes wrong in data work goes wrong in the first meeting, quietly, with both sides sure they agreed. Six sessions on running that meeting as an AI developer: the six doors every discovery conversation has, why current way is the one this role opens widest, the plain second sentence that lets a business person learn how data work thinks while she answers, and a bench that puts one invented operations director with 24 hidden facts in your browser and counts what each way of asking is worth.

6sessions
6doors
24hidden facts
5ways of asking, counted
45min per session

The six sessions 🎯 · from "can AI answer the WhatsApps" to a brief she can read

The running case is Harbourline, an invented chain of 38 pharmacy and clinic outlets across Singapore and Malaysia, and its operations director Adeline Tan, who has never heard the word pipeline. Every fact on her sheet is printed in the bench's bank file; the course claims the mechanism, never the numbers as facts about pharmacies.

🀝 Session 1 · core

The gap, from the AI developer's chair

Why "can AI answer the WhatsApps" is a request about a workflow nobody has watched, the current-way door opened widest, and the split every assistant rests on: lookups the assistant does, decisions a person keeps.

β–Ά Start here
πŸ—‚οΈ Session 2 Β· core

The thread end to end, and its data

One real thread watched from the first message to the OK, then where each half lives: supplier chats, outlet chats in three languages, no order table, a product list with the wrong names.

πŸŽ›οΈ Session 3 Β· bench night

The AI developer's questions, and the bench

Five kinds of question and the same operations director run five ways. The fast interview scores 21 and writes down "reply automatically"; the doors in order 54; current way widest, 55.

β˜… the bench
πŸ’¬ Session 4 Β· core

Teaching while you ask

The one concept worth ninety seconds in an AI developer's meeting: an assistant drafts the lookups and a person keeps the decisions. Twelve teach-back lines rewritten for a person who has never seen a model.

🌱 Session 5 · core

Three projects, and the assistant that only drafts

Her pains become three candidates, and the first is a log, not a bot. Then an assistant that drafts the plain OKs for one manager and four suppliers, and never approves a substitute.

πŸ“„ Session 6 Β· capstone

The mock meeting and the one-page brief

A full run on the bench with your own sheet, scored, then the brief she can read: the workflow in her words, what the assistant will never decide, the visit-log test. Final scorecard.

πŸ”’ final scorecard
core bench night capstone

Your passport 🎫

Clear all three quiz questions in a session and it gets stamped. Six stamps means you can walk into a meeting with a business person who knows nothing about data, leave with the decision, the current way and the real data state, and send a brief she can read the next morning. Stamps live in this browser only.

Four chairs at the same table πŸͺ‘

The same framework, the same company and the same bench engine, built four times for four roles. Each course marks a different door to open widest and carries its own question bank and fact sheet. The framework itself lives in the data analyst course's session 1; this course links to it.

What this is not, so you land in the right place 🧭

If your question isGo here instead
I am the executive. How do I read a number with confidence and brief an analyst?Data Literacy β†—
I have been handed a question. How do I sharpen it and say what the data can and cannot answer?Data Thinking β†—
How do I present findings, handle a room, and influence a decision?Communication β†—
How do I run product discovery as a discipline, week after week?Product Thinking β†—
How do I frame a decision properly, with options, evidence and a call?Decision Intelligence β†—
What is a data maturity model, and how do I run a real assessment?Governance 101 β†—
I am the data person. I have 45 minutes with a business person who knows nothing about data, and I need to leave with something I can build.you are in the right place

The first meeting, run by the data side. The decision, the current way and the real data state, got out of a person in words that teach her something as she answers. Reading numbers, sharpening a handed question, presenting, and discovery as a product discipline are each taught once, in the course that owns them, and linked from here rather than repeated.

Choose your path πŸ—ΊοΈ

Three doors into the same conviction: the way of asking, not the person across the table, decides what you leave with.

πŸšͺ I have a meeting on Monday 1β†’ 3β†’ 6 the sheet, the rehearsal on the bench, the brief you send the next morning
🀝 I keep getting asked to add AI 1β†’ 2β†’ 5 the workflow behind the request, where each half of it lives, three projects starting with a log, not a bot
🎯 The whole meeting 1β†’ 2β†’ 3β†’ 4β†’ 5β†’ 6 from the request as received to a brief she can read, with her learning something on the way

What is honest here 🧾

The company is invented and says so on every page that uses it. The bench is counted from a printed file. Where a page rests on a book or a paper, it says which and how it was read, and where a widely quoted number could not be traced, the page says that instead of quoting it.

ClaimStatus
Harbourline, Adeline Tan, and every fact on her sheetConstructed. Written to be typical of a mid-size retail chain; printed in full in the bench's bank file; never a claim about a real business
Every count on the bench: net value, false beliefs, doors, the 20-minute counterReally computed in your browser from the printed bank, and verified headlessly in node before any page quoted a number
Tappers and listeners: about 50 percent predicted, 3 of 120 namedReported from Heath and Heath, Made to Stick (2007), citing Newton's 1990 Stanford dissertation, which was not read at source
Measurement as a reduction of uncertainty about a decisionHubbard, How to Measure Anything (2014), definition as it appears across summaries; the book was not opened here
Ask about the past, not the future; people say yes to be politeFitzpatrick, The Mom Test (2013). Only his verified wording is quoted; a paraphrase that circulates as a quote is not
The analytics translator role and its predicted headcountRole named from the 2018 HBR article; the headcount figure was not read at source and is not quoted

The knowledge map 🧠

The whole course at a glance - hover a session to spotlight its concepts, click any node to jump in.